


Personal Assistant

by DerekHaleGirl97



Series: Girl!Stiles [12]
Category: Teen Wolf (TV)
Genre: Alternate Universe - Human, Alternate Universe - Office, Always Female Stiles Stilinski, Bondage, Boss Derek Hale, Collars, F/M, Fucking Machines, Gags, Kinda?, Master Derek Hale, Master/Slave, Naked Female Clothed Male, Objectification, Office Sex, Oral Sex, Orgasm Denial, Personal Assistant Stiles Stilinski, Punishment, Rape/Non-con Elements, Rough Sex, Sex, Sex Toys, Sexual Slavery, Slave Stiles Stilinski, Top Derek Hale/Bottom Stiles Stilinski, Vaginal Sex, idk - Freeform
Language: English
Status: Completed
Published: 2020-09-05
Updated: 2020-09-05
Packaged: 2021-03-06 14:14:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,228
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26300251
Author URL: https://archiveofourown.org/users/DerekHaleGirl97/pseuds/DerekHaleGirl97
Summary: Today is the worst day Derek's ever had. Fortunately for him, his Personal Assistant, Stiles, is there to help him out.
Relationships: Derek Hale/Stiles Stilinski
Series: Girl!Stiles [12]
Series URL: https://archiveofourown.org/series/618775
Comments: 4
Kudos: 152





	Personal Assistant

**Author's Note:**

> This was inspired by SinQueen69's "The Best PA". 
> 
> Don't read if the subject matter upsets you. Be sure to read the tags before proceeding.

Derek was about ready to quit his job. Today was possibly one of the worst days he had since he got the promotion to Head of Accounting, and it seemed to be getting worse and worse.

Jackson was an asshole to his staff, having them do little things that had nothing to do with their job, all for his enjoyment. Matt was just downright lazy and incompetent, forgetting to bring essential documents and sending information to the wrong people. He forced the unpaid intern to do most of the work, which wasn’t great because the intern was still new to the job, so of course, they wouldn’t be great. But horrible co-workers weren’t the least of his problems. His computer has been acting up all day, and if it weren’t for the help of his PA, he wouldn’t be able to send the appropriate files to his boss. 

And of course, there were smaller things like forgetting to add sugar to his coffee, getting ketchup on his new white shirt when it dripped from his burger during lunch, and running ten minutes late to a meeting after Matt forgot to inform him about it. Derek hated how upset his PA got when she realized there was a meeting. Stiles prides herself on being punctual and having all the information needed to help Derek, especially when he’s busy today. He did his best to let her know that it wasn’t her fault and that she was still his best assistant. 

All in all, this day was the worst.

Derek had just sent the last of his emails when he felt the frustration get to him. With a sigh, he loosens his tie a little and picks up his phone to call Stiles.

“Hello, Mr. Hale, how can I help you?” Stiles responds, professional as she can be.

“Stiles, may you come to my office? There is something we need to discuss.”

“Yes, sir. I’ll be there in a minute.” 

Derek hangs up the phone, checking one last time to see if he had any new emails to respond to before setting his computer to sleep mode. 

Stiles comes in, shutting the door behind her before going to stand in front of his desk. “What do you need help with, Mr. Hale?”

“Stiles, I want to take a break. Are there any appointments that I need to deal with right now?”

She shakes her head, “No, sir. You’re free for the rest of the afternoon. Unless Mr. Daehler forgot yet another meeting.”

Derek smiles, “No. He’s fucked up enough today. I’m sure he’ll be more punctual from now on.”

“Hopefully,” Stiles returns his smile. “There is nothing else that needs to be attended to right now, sir.”

“Good. Clear your schedule, Stiles. I plan for you to stay with me for the rest of the day.”

“Yes, Mr. Hale. Give me a moment to step out and have Lydia take over.”

Derek nods, and Stiles steps out. He takes the time to close the blinds and rummage through his drawers for the things he needs. Everything is set up by the time Stiles returns. She makes sure to lock the door behind her, and Derek quickly sends a message to his colleagues to not disturb him for the rest of the hour. Stiles stands by the desk again, and Derek takes a moment to admire her outfit. Today, she chose to wear a white button-up shirt, a tight pencil skirt, black stockings, and black high heels. Her hair was done up in a perfectly combed bun, and a pair of black-rimmed glasses were perched on the bridge of her nose. Everything about her screamed professionalism, but Derek knew there was a side to her that was willing to shed the look for something more… inviting. 

“What would you like to do, Mr. Hale?” Stiles asked, more flirtatious than professional. Derek’s smile grew as he removed his jacket and tie.

“Come here and sit on my desk,” he says, tapping his hand against the top. He’d already cleared it, so there was plenty of room for Stiles.

She smirks in response, walking over and jumping up to sit. Derek immediately stands, placing his hands on her knees to spread them out as he goes between them. When he’s flushed against her, his hands move to her waist, pulling her even closer.

“My day has been horrible so far. Would you mind helping me out by making it better?” Derek couldn’t help but ask, staring deep into her whiskey eyes.

“Of course, sir,” Stiles smirks, reaching up to unbutton her top. Derek grabs her hands before she can do so, his smile wide. 

“Let me,” he says and starts to unbutton it for her, revealing a black lacy bra that was see-through. Derek’s dick twitches at sight, and he can’t help but kiss her, deep and hungry.

“Did you wear these for me?” He finishes her shirt, pushing it off her shoulder while getting an eyeful of her chest. Derek peppers kiss across her skin as Stiles keens. 

“Only the best for you, sir.” Stiles breathes, her leg moves to brush against his thigh. 

“I wonder what else you’re hiding underneath,” Derek nearly purred, his hands slowly gliding down to her skirt. Stiles’ breath hitches when he begins to work on her zipper.

“I think you might like what you’re about to see,” Stiles starts panting when Derek pulls off the skirt. Underneath, she was wearing matching panties made from the same material as the bra. Her stockings stopped around her thigh and held in place with a garter belt. He nearly whimpers at sight; she was so beautiful that she could make him cry. 

Derek dives in for another kiss, pulling her even closer by wrapping her legs around his waist. He devours her mouth, thrusting his tongue between her lips. “So beautiful,” he says between kisses, “I could fuck you right on this desk.”

“Why don’t you?” Stiles smirks mischievously, her fingers combing through his hair. “I’m all yours. Nothing is stopping you.”

Derek growls, pushing her back until she is lying down, and he goes back in for another kiss. They make out for a few minutes, not coming up for air until they are gasping for breath. He releases her hair from the bun, letting the ringlets fan out before moving onto her neck. While coloring her neck with bites and bruises, one hand reaches past the panties’ waistline, pressing his fingers against her clit. He’s pleased to discover that she still has the dildo he inserted that morning. Derek grabs the toy and begins fucking her with it, making her moan out as her nails rake against his clothed back. 

He travels down her neck toward her chest, pulling the bra down to reveal her sizable breasts and begins to mark them as well, running his tongue over her nipples, gently biting her buds until they pebbled. All while he was thrusting the dildo in and out, causing her to cry and moan from the pleasure.

“Look at you,” He goes back up to breathe against her ear. “You’re coming apart so beautifully. You’re a needy little cock slut, aren’t you?”

“Yes, sir, yes!” She gasps, yelping when Derek bites her neck hard. “So needy, only for you! Ah!”

Derek pulls back, quickly flipping her on her stomach and adjusting her until he had her bent over the edge. He unhooks her bra, slipping the flimsy fabric down her arms, then tosses them to a corner of the room. The panties follow, leaving her naked save for the stockings, garter, and heels. He takes her glasses off, placing them in a drawer so they wouldn’t fall over.

“Hands behind your back,” Derek commands, grabbing a fist full of her hair. 

Stiles gasps but follows his orders. Derek grabs her wrists, keeping them together as he reaches over into his desk to grab the handcuffs. They were thick and made of leather with a short chain between them. Once the cuffs are locked in place, he reaches again for the matching collar. He slips it around her neck, tightening it until it was snug, then producing a small lock from his pocket to fix it in place. The o-ring that hung from the front was a little tag that read ‘Stiles Hale - Personal Slave.’ Derek finishes her ‘outfit’ by clicking a leash to her collar, wrapping the free end around his hand.

“Whose bitch are you?” Derek asks, yanking on her leash so she would tip her head back.

“Yours, sir. I’m your bitch.” Stiles gasps, straining a bit in her restraints.

“Good.” He kisses her, then nudges Stiles’ legs apart, fixing them in place by the corners of his desk to keep her wide open for him. With Stiles fully restrained, he removes the dildo, slowly pulling it out to scrap against her sensitive walls. Stiles cries out, her breath hitching as each brush sends a wave of pleasure through her body. 

Derek slaps her ass, making her yelp in surprise. “Hush, baby girl. You don’t want everyone to know what we’re going in here, do you?”

“No, sir,” Stiles blushes at the idea of people hearing her cries. 

“Stay quiet, and if you can, I’ll give you a treat.”

Stiles bites her lips as a response. Derek knew that if she had her hands free, she would make the locking motion and pretend to throw away the key. 

With that, he continued to pull the dildo out until it finally left her pussy, trailing a small line of cum and lube in its departure. Derek then pushes his fingers inside her hole, stretching her out a little more while his thumb plays with her clit. Stiles forces herself not to make noise, making little punched breaths of air as he starts to pump his fingers. After a minute or so, he pulls out his erect cock and slots it into Stiles’ hole, groaning at how wet and tight she was around him. Stiles gasped at the intrusion, biting her lips while Derek slowly began to thrust.

Derek closes his eyes, yanking the leash harder as he picks up his pace. With all the stress and frustration, he can finally take it out on her, pounding her over and over as only the noise of skin slapping skin fills the room. Derek digs his fingers into her hips, making her meet his thrusts. He groans out how beautiful she was and how good she makes him feel, all while trying to tear her in half. Stiles struggles to keep herself quiet, but with Derek practically fucking her into the desk, it’s getting harder to resist screaming. She can’t even keep her yelps quiet as his cock brushes the sweet spot in her pussy. 

“Such a good little whore,” He pants, “you love being fucked like a bitch, don’t you?”

“Yes! Yes, master, I love it so much.” Stiles nearly screams out, but her voice is so tight that he can barely hear her. “I love being your bitch! Please, please fill me with your cum!”

“Since you asked so nicely,” Derek chuckles, then presses his cock deep inside, letting himself explode inside her walls.

This time, Stiles couldn’t help but cry out, cumming alongside Derek. Before a good scream could ring out, Derek had to clamp his hand over her mouth to silence it. He had to stop and listen in case someone was coming. After a while, no one came, and Derek sighed. Turning his attention back to Stiles, he uses his free hand to land a hard slap on Stiles’ ass, making her yelp as she felt the sharp sting.

“You stupid cunt, I told you to be quiet.” Derek sneers, smacking her ass again and again. Stiles cried out from the pain, struggling against Derek, but her restraints held her firm, and she could do nothing but take the beating. “If you won’t shut up, then I’ll just have to make you.”

Keeping his hand clamped over her mouth, he yanks her up with him, all while keeping his cock up in her pussy, and opens one of his drawers and pulls out a ball gag. He rarely had to use it, but it came in handy whenever Stiles decided to disobey. Besides, he liked the look of ball gags on her. 

“Open,” He demands, moving his hand so Stiles can open her mouth. Her lips barely parted when he forces the rubber ball to slip in between her teeth. Derek pulls the straps tightly around her head, stretching her jaw a little, and buckling the gag. Stiles whined into the ball gag, trying to adjust her jaw to get comfortable. Derek cruelly laughs, reaching around to slap one of her tits before pushing her down on the desk. He puts his hand on the back of her neck to pin her down as he works himself up by fucking her again. Stiles is much slicker, already lubed up with his cum.

“You’ll be wearing that for the rest of the day,” Derek decides, letting go of the leash to grab her hair instead, yanking her head up, so she is arching her back. “Until I say otherwise, understand?"

Stiles nods, whimpering as Derek snaps his hips against her, keeping her pinned while he uses her as a fuck toy. Raming her hard without taking a moment to ease up or work her up. She didn’t deserve to cum anytime soon, and he loved to just mindlessly fuck her for his pleasure. That’s what she was there for, for him to use her however he liked. He could have kept her at home, strapped to a machine, or something just to wait for him to come home and fill her up with nothing but his cum.

Eventually, Derek is orgasming again. This time he pulls out and paints her beautiful ass with his cum, then wiped himself between her cheeks. 

“What should we do with you now?” Derek asks, taking in the sight he made. Stiles was so beautiful, so vulnerable that he was only lucky to have. He goes behind her again, grabbing, groping, and messaging the cum into her ass, thinking of what to do next. After all, she still needs to be punished, and Derek’s got twenty minutes until his break is over.

“You haven’t had a good spanking, haven't you, Stiles?” Derek says, pinching her ass to make her yelp. He reaches into the desk, rummaging through until he pulls out a paddle. It’s heavy, made of wood with holes drilled in the flat part. It was something he had gotten for moments like these. He knew Stiles enjoyed being spanked, but he didn’t want her to enjoy it as he marked her ass. This paddle was guaranteed to bring more pain than pleasure.

He doesn’t give Stiles a warning when he hits her ass with it. The gag thankfully mutes stiles’ cry, and her cheeks turn a pretty pink. The paddle falls again, making her jerk in place. The second hit must sting because of the tears running down her face. However, instead of trying to tell him to stop, she just bites the ball gag and braces herself for the next one. To test it, he hits her again, and she barely makes a squeak. Derek smiles, giving the paddle another snap.

“Does it hurt, sweetie?” Derek asks rhetorically, hitting her once more. Her ass was turning a bright red, with lines forming where the paddle’s edges impacted her soft flesh. “Maybe next time, think twice before you disobey your master.”

The paddle came down on her multiple times, slapping her ass repeatedly until Stiles was a mess. Trembling and silently sobbing as the pain became too much. Once Derek knew she had enough, he let the paddle fall from his wrist and took his cock out from where it was straining against his pants. He uses this opportunity to satisfy himself again, knowing Stiles would be in too much pain to get any pleasure from him stuffing his cock in her. She even whines when Derek pushes into her hole, going pliant as he starts to thrust.

“Doesn’t this feel good? Don’t you love this?” 

Stiles is mostly moaning and sobbing, still in too much pain to enjoy the way Derek was pounding her. 

“That’s it!” Derek huffs, trying to press even deeper. “This is all you’re good for, isn’t it? You’re only good to be a cum dumpster and a cock slut. A little breeding bitch who is only hungry for my cock.” He snaps his hips one last time, and then he starts cumming for the third time. 

Derek stands there for a moment, riding off his high and catching his breath. Stiles is squirming a little beneath him, trying to find some relief to the ache in her pussy. Once he’s calm down, he pulls out of her and watches some of his cum dribbles from Stiles’ hole. He checks the time and realizes that his break is ending in five minutes. 

“Looks like we’re almost out of time. Unfortunately, I can’t let you get back to work when I still need to punish you.” Derek says, rubbing a gentle hand over her ass, making sure to rub his cum into her skin some more. “You’ll just have to spend the rest of the day in my closet until it’s time to go.”

Derek changes the handcuffs to tie her arms in a box tie, making sure to secure it with a breast harness against her back so she couldn’t move them. Then he unties her ankles from the desk’s legs, taking her leash, then tugging her to the closet. She follows him on shaky feet into the small space where she sees the old fucking machine. Derek sees her eyes widen, knowing that she knew what he was going to do. He just ignores her muffled protests as he brings her over to a small stool, bending her over it, then tying her leash and legs to it to keep her in place. 

“This should keep you entertained while I work,” Derek says, positioning the machine, so the dildo lined up with her cunt. “You’re still not allowed to cum, so I better not see this hole soaked. Right now, your pussy is only for my cum. If I see it anymore wet, I’ll leave you here overnight with it on full blast.”

He eases the dildo into Stiles’ hole, pushing only the head past her pink lips before securing the machine in place. Once that was done, Derek switches on the fucking machine and taking a moment to watch Stiles attempt to free herself from the contraption. She whines again, trying to lean away from the rubber cock as it slowly pushes in and out.

“Be good now, sweetie,” Derek says, pressing a kiss to her forehead before grabbing a blindfold in one of the shelves and placing it over her eyes. “Remember, no cumming and so noises until I’m finished.”

With that, Derek shuts the door to the closet, trapping Stiles inside as the machine whirled on. 

***

The day got easier from then on. The IT guy fixed his computer and even updated the software to connect to the office’s internet. Derek was able to work in peace, finishing up with an hour or so left in his shift. All the while, he had the sound of Stiles’ soft whimpers coming from the closet to give him some background sound to listen to as he worked. 

With the last email of the day sent, Derek made his way over to the closet to check on Stiles. She’d long since stopped whining, looking almost asleep as the fucking machine switched between barely pulling out to pistoning into her pink hole. Just as Derek hoped, she was still dry, with the only witness being his drying cum. 

“Such a good girl,” Derek praises, shutting the machine off and running his hand over her back. Stiles whines in relief, falling limp against the stool. “There, there,” he presses a kiss on the small of her back. “You did so well, sweetie. Relax for a bit before I finish our session.”

Stiles weakly nods, letting her head rest against the stool. Derek presses another kiss, getting up to clear his desk. Making sure she had some water and feeding her some snacks he kept in his office. He gave her a minute before finally letting her up from the seat. Derek brings her back to the desk, having to guide her as she is still wearing the blindfold. He placed her back in the same position to put the dildo back in its place. She gasps, shuttering as the toy is slipped back into her sore pussy.

“I think your cunt has had enough attention,” Derek says, patting the toy in place. “I want to use your mouth instead.” He makes her kneel on the floor and removes the ball gag, messaging her jaw as it leaves her mouth. “You’re still not allowed to talk,” he reminds her, “It only has one use right now.”

Stiles nods again, dropping her mouth as Derek pulls his cock out. He smirks, then slides into her waiting mouth, moaning softly as her lips wrap around him. Derek begins thrusting into her mouth, purposefully forcing his cock down her throat to listen to her gag. He keeps a tight grip on the leash, holding her head in place while fucking into her mouth. Derek removes the blindfold, watching as she blinks her eyes to adjust to the lighting. He loves the way she looks up at him while his cock fills her mouth. As he picks up the pace, his phone rings, making him pause to pick it up while also pressing his dick down her throat.

“This is Hale.”

“Nephew,” Peter responds cheerfully. “No need to be formal with me.”

Derek sighs, “Why are you calling me at work? I was just getting ready to leave.”

“Yes, I know,” Derek could hear his uncle rolling his eyes. “I just wanted to know where Stiles kept her files on that meeting.”

“The one from this morning?” Derek asked, once again, picking up his pace when he notices Stiles’ face turning red. He pulls the phone from his face, holding it against his chest as he stares down at her. “Breathe, you dumb slut.”

Stiles whines softly but does her best to breathe through her nose.

“Yes, the one Daehler conveniently forgot. I just sent her some files to give to you, but Ms. Martin just told me that she took over for Stiles. My computer just broke down, so Stiles has the only copy of the files left.”

“How unfortunate,” Derek says, trying to hide the breathiness in his voice. He fucks her mouth harder. “I’ll have to talk to her later. She’s busy right now and won’t have access until tomorrow. Do the files need to be turned in?”

“Not for another week,” Peter admits. “Tell Stiles to send them back to me as soon as she can. I know how busy she can get as your PA.”

“Right,” Derek forces himself not to groan as he gets closer to his climax. “I’ll call you later.”

“Alright. Tell Stiles I said hi.”

With that, Derek hangs up just in time to cum. He almost screams in relief as he shoots down her throat, still thrusting against her as he rides through his orgasm. Stiles is forced to swallow his cum, tears pricking her eyes as she chokes.

“You did such a good job,” Derek pants, pulling out of Stiles and cleaning his cock by wiping the cum on her face. “You learned your lesson, haven’t you?”

Stiles nods, not saying anything. 

“Good.” Derek slips the ball gag back into her mouth, this time he locks the straps, preventing anyone from removing the ball gag unless they had a key. He does the same to the collar before untying Stiles’ arms to put her clothes back on. Derek only lets her put on the top and skirt, keeping the panties and bra stored in his messenger bag. Once she’s done, Derek cuffs her hands behind her back and adds a pair around her ankles with enough length to walk. 

“There,” Derek says, placing a kiss on her lips. “As a proper slave should be.”

Derek spends a minute collecting their things, then he grabs her leash again and leads her out of his office. All the other employees are still working, not paying Stiles or Derek any mind as they leave the building. Even though people barely notice Stiles anymore, Derek still loves to show off his slave. He sees how Matt and Jackson stare after them with envy, knowing how much they wanted Stiles but knew she was off-limits to them. It’s against the rules to go after a co-worker’s slave. And because they were such assholes, Derek didn’t mind flaunting her around dressed like this as they left.

Honestly, he was glad to have her around, whether as his PA or his sex slave. Thanks to Stiles, his day didn’t end as horrible as he had expected. 

He’ll just have to reward her when they got home.


End file.
